Azo dye.



i s i z HANS FREIMMEN, 31 STQUZ'ZIEM, NEAR LD'O'SSELKZ GRZ, i

.ureas (see the German patentspecification 11 3200 and 123693). Snch prorincts have either a symmetrical or unsymmetrical form according to Whether two similar or two flpecificstioz: of Letters Application filed February 3 1810. serial MLQQS.

the carbonyl. group and yield valuable mono anal disco (lyes. The only case extent in which an unsymmetrical urea been produced by the reaction with phosgen, is by reaction with 2:2") amidonophthol-7-sulonic acid enri p-emitioacetenilid which only comhines with one molecule of a (iiazo compound (see German Patent 148505).

It has now been discovered thot the sulfoniceciris of any m-rlismin of the henzol group inrier the action ofphosgen unite with the em!donephthol-sulfomc-acids, 1n Wll'lCll the hydroxyl and mud groups are in neither the ortho nor the pore position with regard to one another, and form a double nrec. Thus from one molecule of tolnyleno clisniin-sulfonic acid 1 :53 6 l and two molecules of 2 5-omirlo-nephthol-Z-sultonic-ecicl, the following double is ohteicQd.

These new substances may oomhinerl with. two molecules of iiazo compound to form at valuable orange to bluish recl dye which cots directly on cotton 21116 is proof orgsiiic ocicls and diluted mineral ccicls. Organic ecitls are Without influence to the dyestiiifs and even against dihitctl mineral acids rior one.

Of the isomeric toluylene-diemin-sulfonic is preferable for conciensetion with an1i lo-- naphthol-sulfonic acid which is nrohahly clue to its symmetricei construction. The clyes proainced from this new product of the condensation of this acid with phosgen and 2:5 emifioncphthol-Tsulfonic acitl'are charecterizecl over the corresponding products derived from csrhonyLclioxy-clinophthylzimin-sclfonic-ecicl according to German Patent ll'o. 116,200 by their brighter and more yellow shoalsw These dyes are also characterized by] their great intensity of color solubility in water.

E o diictsfi solution sothe fastness remains a supe- (licm memes the new eco (Eyes, according, to the present invention, sapomiiecl. If the product of the reaction 18 then ecidulatcd "with sulfuric acid, and filterecl hot, the azo substances of the emit-lo nephtholshlionic acicl remain ioehind in the filter,

and toluylene(liamiii-sultonic acid may "be traced in the filtrate.

The material from which the new dyes are prorlucecl, Wes hitherto unknown and may he prodncetl as follows: A mixture of 24 2:5 smiclo-naphthol-Y-sulfonic acid. 10 lrgs. 1:2:tz toluylene-cliamin-sulfonic rciri, and 40 kgs. of ce-lcinaterl socls, is dis solved in 280 to 25?) liters of Water. Plies gen gas is then passed slowly through the solution which is kept at ordinary temperet'ores, and stirred, and this is continued until the reaction is complete, that is, until the reacting mixture Will. not react with e nitrite. The new precinct portly precipitates out as a grayish sa ntly cleposit. Whom on the other hand, co rbonyl-dioxydinaphthylsmin-disulfosic acid is proclucecl 'under' analogous concli found sitter e" a short time.

ons s jelly-lilac sulistonce" on left standing for has the above formula by the fact that the condensation and the formation of the dye only-proceed smoothly when the original substances from which itis made are used in the quantities corresponding to the above formula' v I l The following are some examples of the dyes produced from the product of the con densation described above:

Example I: Azdiazo solution obtained in the .known manner from 10.7 kgs. ofotcluidin is combined with the product of the condensation described above, which has been brought into the form of solution :by 'meansoflan excess of soda} After12 hours the hot solution of the dyestufi' is precipitated with salt, pressedand dried. The dye colors cotton in bright orange red shades without requiring a mordant.

Example II: To 88.8 kgs. of sulfo-m' toluylene-diamindicarbonyldioxydinaph thylamin-disulfonic'acid there'is added while consisting'i'n the condensation of one molewith two molecules of adiazo compound.

with two molecules of diilerent diazo comand combining the product of condensation consisting in the condensation of one molecule stirring well, a diazo solution prepared from 'o-anisidin.

,. diazo. compounds.

28.6 kgs. beta-naphthylamin.

4;. The process for producing an azo dye consisting in combining suliio-m-toluylenet go pounde 7 5. The process for producing an azo dye cule of toluylene diamin sulfonic acid. 1 2 6 4 with phosge'n and two molecules of amido naphthol su'lfon'ic acid 2 5 7 with two molecules of a diazo compound.

'6. The process for producing an azo, dye

of toluylene diamin sulfonic acid 1:226:42 withphosgen and two molecules of amido na phthol sulfonieMa-eidj 2: 5 :7 and combining the product of condensation with two molecules of different diazo compounds.

The product is soon completed. These- 0.

lution of dye is then boiled, precipitated with salt, pressed and dried. ,Unmordanted cotton will be colored in bright bluish red shades by means of this dye'stuif. The dye is also much more intensive and brilliant 35 than the product derived from carbonyl- 'dioxy-dinaphthylamin-disulfonic acid (see German Patent No. 122,904). 3A similar dyestuff may be obtained from "Two molecules also be used for-combination.

I claim :-4 i

'. 1. The proc'essfor producingan ago dye consisting in combining sulfo-m-d1am1n '45 'dicarbonyldioxy dinaphthylamin disulfonic-acid with two molecules of a diazo compound.

2. The process for-producing-an azo dye consisting in combining a sulfo-m-diamin- 5O dicarbonyl dioxy dinaphthylamin disul-' fonic-a'cid with two molecules of different 3. The process for producing an azo dye consisting in combiningsulfo-m-toluylene- 55 d amin dicarbonyl dioxy dinaphthylamindisulfonic acid having the formula J t k o r diamin-dicarbon'yl dioxy dinaphthylainindisu'lfonic acid having the formula 7. The process for producing an azo dye consisting in mixing 24 parts of amidonaphthol-sulfonic acid 225:7, 10 parts of toluylene diamin sulfonic acid 1 t 2 :6 4

and 40 parts of calcined soda, dissolving the .85

mixture in 200 to. 250 parts of water, passing phosgen gas through the solution at ordinary temperature and stirring, and combining the resulting product of the condentwo molecules oi? diazo comsation with pound.

8. The process for producing an azo dye consisting invmixing 24. parts of amide; naphthol-sultonic acid 2:5:7, 10 parts of toluylene-diamin-sulfonic aci.d 1:256:41

and 40 parts of calcined soda, dissolving the mixture in 200 to 250 parts of water, passof difi'erent 10 fdiazo compounds may in the known manner l0 to directly color cotton orange to blue red and being characterized by their solubility in water and intensity of color and being proof against organic acids and dilutedmineral acids.

10. As. new products, the azo dyes which contain, as a middle component, a sulfo-mdiamin dicarbonyl dioxy dinaphthylamin-disulfonic acid nucleus, said dyes being adapted to directly color cotton orange to blue red and being characterized b their solubility in water and intensity 0 color and being proof against organic acids and diluted mineral acids.

11. As new products, the azo dyes which contain as a middle component sulfo-mtolu lene diamin dicarbonyl T dioxy dinap thylamin-disulfonic acid having the formula said dyes being adapted to directly color 30 cotton orange to blue red and being characterized by their solubility in water and intensity of color and being proof against organic acids and diluted mineral acids.

In witness whereof I have hereunto set my hand in the resence of two witnesses. HA S FREIMANN. [1,. 5.]

Witnesses:

O'ITO Komo, CHAS. J. Wmon'r. 

